Epibatidine: Impact on nicotinic receptor research

Cellular and Molecular Neurobiology

Volumn 23, Issue 3, 2003, Pages 365-378

  Dukat, Małgorzata ^a   Glennon, Richard A ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Cholinergic receptors; Epibatidine; Epiboxidine; Nicotine

Indexed keywords

6 ETHYLNICOTINE; 6 METHYLNICOTINE; A 84543; ACETYLCHOLINE; CHOLINERGIC RECEPTOR; EPIBATIDINE; EPIBOXIDINE; ISONICOTINE; NICOTINE; NICOTINE DERIVATIVE; NICOTINIC RECEPTOR; NORNICOTINE; UNCLASSIFIED DRUG;

ARTICLE; CENTRAL NERVOUS SYSTEM DISEASE; DRUG STRUCTURE; HUMAN; PHARMACOPHORE; PRIORITY JOURNAL; RECEPTOR AFFINITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINE; ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; BINDING, COMPETITIVE; CENTRAL NERVOUS SYSTEM; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEURONS; NICOTINE; PYRIDINES; RECEPTORS, NICOTINIC;

EID: 0037871490     PISSN: 02724340     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1023692705700     Document Type: Article

References (59)

1. Abreo, M. A., Lin, N. H., Garvey, D. S., Gunn, D. E., Hettinger, A. M., Wasicak, J. T., Pavlik, P. A., Martin, Y. C., Donnelly-Roberts, D. L., Anderson, D. J., Sullivan, J. P., Williams, M., Arneric, S. P., and Holladay, M. W. (1996). Novel 3-Pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors. J. Med. Chem. 39:817-825.
2. Arneric, S. P., and Brioni, J. D. (1999). Neuronal Nicotinic Receptors: Pharmacology and Therapeutic Opportunities, Wiley, New York, pp. 271-284.
3. Badio, B., and Daly, J. W. (1994). Epibatidine, a potent analgetic and nicotinic agonist. Mol. Pharmacol. 45:563-569.
4. Badio, B., Garraffo, H. M., Plummer, C. V., Padgett, W. L., and Daly, J. W. (1997). Synthesis and nicotinic activity of epiboxidine: An isoxazole analogue of epibatidine. Eur. J. Pharmacol. 321:189-194.
5. Badio, B., Garraffo, H. M., Spande, T. F., and Daly, J. W. (1994). Epibatidine: Discovery and definition as a potent analgesic and nicotine agonist. Med. Chem. Res. 4:440-448.
6. Badio, B., Shi, D., Garraffo, H. M., and Daly, J. W. (1995). Antinociceptive effect of the alkaloid epibatidine: Further studies on involvement of nicotinic receptors. Drug Dev. Res. 36:45-59.
7. Beers, W. H., and Reich, E. (1970). Structure and activity of acetylcholine. Nature (London) 225: 917-922.
8. Brown, L. L., Kulkarni, S., Pavlova, O. A., Koren, A. O., Mukhin, A. G., Newman, A. H., and Horti, A. G. (2002). Synthesis and evaluation of a novel series of 2-chloro-5-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-3-(2-(4-pyridinyl) vinyl)pyridine analogues as potential positron emission tomography imaging agents for nicotinic acetylcholine receptors. J. Med. Chem. 45:2841-2849.
9. Campillo, N., Paez, J. A., Alkorta, I., and Goya, P. (1998). A theoretical study of epibatidine. J. Chem. Soc. Perkin Trans. 2:2665-2669.
10. Carroll, F. I., Lee, J. R., Navarro, H. A., Brieaddy, L. E., Abraham, P., Damaj, M. I., and Martin, B. R. (2001b). Synthesis, nicotinic acetylcholine binding, and antinociceptive properties of 2-exo-2-(2′-substituted-3′-phenyl-5′-pyridyl)-7- azabicyclo[2.2.1]heptanes. Novel nicotinic antagonist. J. Med. Chem. 44:4039-4041.
11. Carroll, F. I., Liang, F., Navarro, H. A., Brieaddy, L. E., Abraham, P., Damaj, M. I., and Martin, B. R. (2001a). Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 2-exo-2-(2′-substituted 5′-pyridinyl)-7-azabicyclo[2.2.1]heptanes. Epibatidine analogues. J. Med. Chem. 44:2229-2237.
12. Chen, J., Zhan, C., Stevens, E. D., Izenwasser, S., Wade, D., Chen, S., Paul, D., and Trudell, M. L. (2002). Synthesis and biological evaluation at nicotine acetylcholine receptors of N-arylalkyl- and N-aryl-7-azabicyclo[2.2.1]heptanes. J. Med. Chem. 45:3041-30477.
13. Cheng, Y.-X., Dukat, M., Dowd, M., Fiedler, W., Martin, B., Damaj, M. I., and Glennon, R. A. (1999). Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepine and related ring-opened analogs at central nicotinic receptors. Eur. J. Med. Chem. 34:177-190.
14. Curtis, L., Chiodini, F., Spang, J. E., Bertrand, S., Patt, J. T., Westera, G., and Bertrand, D. (2000). A new look at the neuronal nicotinic acetylcholine receptor pharmacophore. Eur. J. Pharmacol. 393:155-163.
15. Daly, J. W. (1995). The chemistry of poisons in amphibian skin. Proc. Nat. Acad. Sci. U.S.A. 92: 9-13.
16. Daly, J. W., Garraffo, H. M., Spande, T. F., Decker, M. W., Sullivan, J. P., and Williams, M. (2000). Alkaloids from frog skin: The discovery of epibatidine and the potential for developing novel non-opioid analgesics. Nat. Prod. Rep. 17:131-135.
17. Damaj, M. I., Tucker, S. M., Aceto, M. D., and Martin, B. R. (1994). Analgesic activity of epibatidine and its enantiomers in a chemical model of pain. Med. Chem. Res. 4: 483-492.
18. 125I]IPH, an epibatidine analog, binds with high affinity to neuronal nicotinic cholinergic receptors. J. Pharmacol. Exp. Ther. 282:445-451.
19. Decker,M. W., and Meyer, M. D. (1999). Therapeutic potential of neuronal nicotinic acetylcholine agonists as novel analgesics. Biochem. Pharmacol. 58:917-923.
20. Decker, M. W., Meyer, M. D., and Sullivan, J. P. (2001). The therapeutic potential of nicotinic acetylcholine receptor agonists for pain control. Expert Opin. Investig. Drugs 10:1819-1830.
21. 18F]N-methyl-NFEP: Kinetics, nicotine effect, and toxicity. Nucl. Med. Biol. 26:139-148.
22. Dukat, M. (1994). 208/210 a.k.a. Epibatidine. Med. Chem. Res. 4:433-439.
23. Dukat, M., Damaj, M. I., Glassco, W., Dumas, D., May, E. L., Martin, B. R., and Glennon, R. A. (1994). Epibatidine: A very high affinity nicotine-receptor ligand. Med. Chem. Res. 4:131-139.
24. Dukat, M., Dowd, M., Damaj, M. I., Martin, B., El-Zahabi, M. A., and Glennon, R. A. (1999). Synthesis, receptor binding, and QSAR studies on 6-subtituted nicotine derivatives as cholinergic ligands. Eur. J. Med. Chem. 34:31-40.
25. Dukat, M., El-Zahabi, M., Ferretti, G., Damaj, M. I., Martin, B. R., and Glennon, R. A. (2002). (-)6-n-Propylnicotine antagonizes the antinociceptive effects of (-)nicotine. Bioorg. Med. Chem. Lett. 12:3005-3007.
26. Dukat, M., Herndon, J. L., and Glennon, R. A. (1995). Epibatidine: Reconsideration of the nicotine receptor pharmacophore. NIDA Res. Mono. 162:286.
27. Ellis, J. L., Harman, D., Gonzalez, J., Spera, M. L., Liu, R., Shen, T. Y., Wypij, D. M., and Zuo, F. (1999). Development of muscarinic analgesics derived from epibatidine: Role of the M4 receptor subtype. J. Pharmacol. Exp. Ther. 288:1143-1150.
28. Glennon, R. A., and Dukat, M. (1999). Nicotinic receptor pharmacophores. In Arneric, S. P., and Brioni, J. D. (eds.), Neuronal Nicotinic Receptors: Pharmacology and Therapeutic Opportunities, Wiley, New York, pp. 271-284.
29. Glennon, R. A., and Dukat, M. (2000). Central nicotinic receptor ligands and pharmacophores. Pharm. Acta Helv. 74:103-114.
30. Glennon, R. A. and Dukat, M. (1996). Nicotine recepter ligands. Med. Chem. Res. 6:465-486.
31. Glennon, R. A., Herndon, J. L., and Dukat, M. (1994). Epibatidine-aided studies toward definition of a nicotine receptor pharmacophore. Med. Chem. Res. 4:461-473.
32. Gundisch, D. (2000). Nicotinic acetylcholine receptors and imaging. Curr. Pharm. Des. 6: 1143-1157.
33. Hacksell, U., and Mellin, C. (1989). Stereoselectivity of nicotine isomers. Prog. Brain Res. 79: 95-100.
34. Holladay, M. W., Cosford, N. D. P., and McDonald, I. A. (1999). Natural products as a source of nicotinic acetylcholine receptor modulators and leads for drug discovery. In Arneric, S. P., and Brioni, J. D. (eds.) Neuronal Nicotinic Receptors: Pharmacology and Therapeutic Opportunities, Wiley, New York, pp. 253-270.
35. 11C]Methylated analogues of epibatidine as tracers for positron emission tomographic studies of nicotinic acetylcholine receptors. J. Med. Chem. 41:4199-4206.
36. 3H]Epibatidine binding to nicotinic cholinergic receptors in brain. Med. Chem. Res. 4:538-546.
37. Kim, K. H., Lin, N.-H., and Anderson, D. J. (1996). Quantitative structure-activity relationships of nicotine analogues as neuronal nicotinic acetylcholine receptor ligands. Bioorg. Med. Chem. 4:2211-2217.
38. Koren, A. O., Horti, A. G., Mukhin, A. G., Gündisch, D., Kimes, A. S., Dannals, R. F., and London, E. D. (1998). 2-, 5-, and 6-Halo-3-(2(S)-azetidinylmethoxy)pyridines: Synthesis, affinity for nicotinic acetylcholine receptors, and molecular modeling. J. Med. Chem. 41:3690-3698.
39. Lloyd, G. K., Menzaghi, F., Bontempi, B., Suto, C., Siegel, R., Akong, M., Stauderman, K., Velicelebi, G., Johnson, E., Harpold, M. M., Rao, T. S., Sacaan, A. I., Chavez-Noriega, L. E., Washburn, M. S., Vernier, J. M., Cosford, N. D., and McDonald, I. A. (1998). The potential of subtype-selective neuronal nicotinic acetylcholine receptor agonists as therapeutic agents. Life Sci. 62:1601- 1606.
40. MacPherson, R. D. (2000). The pharmacological basis of contemporary pain management. Pharmacol. Ther. 88:163-185.
41. Meyer, M. D., Decker, M. W., Rueter, L. E., Anderson, D. J., Dart, M. J., Kim, K. H., Sullivan, J. P., and Williams, M. (2000). The identification of novel structural compound classes for neuronal nicotinic acetylcholine receptors and alangesic efficacy in preclinical models of pain. Eur. J. Pharmacol. 393:171-177.
42. Molina, P. E., Ding, Y. S., Carroll, E I., Liang, F., Volkow, N. D., Pappas, N., Kuhar, M., Abumrad, N., Gatley, S. J., and Fowler, J. S. (1997). Fluoro-norchloroepibatidine: Preclinical assessment of acute toxicity. Nucl. Med. Biol. 24:743-747.
43. Nielsen, S. F., Nielsen, E. Ø., Olsen, G. M., Liljefors, T., and Peters, D. (2000). Novel potent ligands for the central nicotinic acetylcholine receptor: Synthesis, receptor binding, and 3D-QSAR analysis. J. Med. Chem. 43:2217-2226.
44. Rupniak, N. M., Patel, S., Marwood, R., Webb, J., Traynor, J. R., Elliott, J., Freedman, S. B., Fletcher, S. R., and Hill, R. G. (1994). Antinociceptive and toxic effects of (+)-epibatidine oxalate attributable to nicotinic agonist activity. Br. J. Pharmacol. 113:1487-1493.
45. Schmitt, J. D. (2000). Exploring the nature of molecular recognition in nicotinic acetylcholine receptors. Curr. Med. Chem. 7:749-800.
46. Sgard, F., Charpantier, E., Bertrand, S., Walker, N., Caput, D., Graham, D., Bertrand, D., and Besnard, F. (2002). A novel human nicotinic receptor subunit, α10, that confers functionality to the α9 subunit. Mol. Pharmacol. 61:150-159.
47. Sharples, C. G. V., Karig, G., Simpson, G. L., Spenser, J. A., Wright, E., Millar, N. S., Wonnacott, S., and Gallagher, T. (2002). Synthesis and pharmacological characterization of novel analogs of the nicotinic acetylcholine receptor agonist (±)UB-165. J. Med. Chem. 45:3235-3245.
48. Sihver, W., Langstrom, B., and Nordberg, A. (2000a). Ligands for in vivo imaging of nicotinic receptor subtypes in Alzheimer brain. Acta Neurol. Scand. Suppl. 176:27-33.
49. Sihver, W., Nordberg, A., Langstrom, B., Mukhin, A. G., Koren, A. O., Kimes, A. S., and London, E. D. (2000b). Development of ligands for in vivo imaging of cerebral nicotinic receptors. Behav. Brain Res. 113:143-157.
50. Sheridan, R. P., Nilakantan, R., Dixon, J. S., and Venkataraghavan, R. (1986). The ensemble approach to distance geometry: Application to the nicotinic pharmacophore. J. Med. Chem. 29:899-906.
51. Spande,T. F., Garraffo, H. M., Edwards, M. W., Yeh,H. J. C., Pannell, L., and Daly, J. W. (1992). Epibatidine: A novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog. J. Am. Chem. Soc. 114:3475-3478.
52. Sullivan, J. P., Briggs, C. A., Donnell-Roberts, D., Brioni, J. D., Radek, R. J., McKenna, D. G., Campbell, J. E., Arneric, S. P., Decker, M. W., and Bannon, A. W. (1994a). (±)-Epibatidine can differentially evoke responses mediated by putative subtypes of nicotinic acetylcholine receptors (nAChR). Med. Chem. Res. 4:502-516.
53. Sullivan, J. P., Decker, M. W., Brioni, J. D., Donnelly-Roberts, D., Anderson, D. J., Bannon, A. W., Kang, C. H., Adams, P., Piattoni-Kaplan, M., Buckley, M. J., Gopala-Drichnan, M. Williams, M., and Arneric, S. P. (1994b). (±)-Epibatidine elicits a diversity of in vitro and in vivo effects mediated by nicotinic acetylcholine receptors. J. Pharmacol. Exp. Ther. 271: 624-631.
54. Tønder, J. E., Hansen, J. B., Begtrup, M., Petersson, I., Rimvall, K., Christensen, B., Ehrbar, U., and Olessen, P. H. (1999). Improving the nicotinic pharmacophore with a series of (isoxazole)methylene-1-azacyclic compounds. Synthesis, structure-activity relationship, and molecular modeling. J. Med. Chem. 42:4970-4980.
55. Tønder, J. E., and Olesen, P. H. (2001). Agonists at α4β2 nicotinic acetylcholine receptors: Structure-activity relationships and molecular modeling. Curr. Med. Chem. 8:651-674.
56. 3H]-N-methylcarbamylcholine. J. Comp. Aid. Mol. Des. 15:247-258.
57. Traynor, J. R. (1998). Epibatidine and pain. Br. J. Anaesth. 81:69-76.
58. Villemagne, V. L., Musachio, J. L., and Scheffel, U. (1999). Nicotine and related compounds as PET and SPECT ligands. In Arneric, S. P., and Brioni, J. D. (eds.), Neuronal Nicotinic Receptors: Pharmacology and Therapeutic Opportunities, Wiley, New York, pp. 235-250.
59. Wright, E., Gallagher, T., Sharples, C. G., and Wonnacott, S. (1997). Synthesis of UB-165: A novel nicotinic ligand and anatoxin-a/epibatidine hybrid. Bioorg. Med. Chem. Lett. 7:2867-2870.